Sodium → HCID 178524407, compound

HRID 1181573Notes

Reaction equation

HRID 1181573 reaction equation
C([N:8]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]1)C1C=CC=CC=1.[Na]>N>[F:19][C:16]([F:17])([F:18])[C:10]1[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 58981242HCID 58981242, compound

Product 1

HCID 178524407HCID 178524407, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

About 50 ml ammonia were condensed into a three-neck-flask in an ethanol-dry ice bath and 100 mg (3.70 mmol) 2-benzyl-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid were added. To the solution sodium was added in small portions until the blue color stayed for more then 5 minutes (about 260 mg, 11.3 mmol). The ammonia was evaporated overnight. Water was added and acidified with 2N HCl solution. The aqueous phase was extracted twice with ethyl acetate, the combined organic phases were dried over Na2SO4, the solvent was evaporated in vacuo to give 560 mg (3.11 mmol, 84%) 5-trifluoromethyl-2H-pyrazole-3-carboxylic acid as a yellow solid that was used without further purification. MS: M=179.0 (API−)

Workup

  1. customcondensed into a three-neck-flask in an ethanol-dry ice bath
  2. custom5 minutes (about 260 mg, 11.3 mmol)
  3. customThe ammonia was evaporated overnight
  4. additionWater was added
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. dry with materialthe combined organic phases were dried over Na2SO4
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-c5fb25e49ad74a0694cd7639daed09fd
Source dataset
uspto-grants-2007_10
Patent number
US07285569B2

Reaction notes

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